Seller’s Journey – “The Soft Stuff is the Hard Stuff”

Selling your business is the most difficult event during a business owner’s journey. Period.

After 25 years advising business owners, I have developed a deep conviction in the phrase that during ownership transition “the soft stuff is the hard stuff.”

I recently attended a client’s 25^th anniversary event filled with music, food, and much emotion. The owner pulled me aside and shared that the sale of his business was going to be harder than he thought. The event showcased his impact on his employees, customers, and even the broader community. More importantly, the pictures, videos and memories highlighted how much his business was a part of him and his family. Clearly, Michael Carlone, the famed character in the 1972 classic The Godfather, was wrong when he famously said, “It’s not personal…it’s strictly business.”

Beyond family, every business relies on a handful of indispensable individuals, whether top executives, sales leaders, or technical experts—who carry disproportionate influence on continuity and performance. Strategic decisions that overlook their role can weaken morale or even threaten the viability of a deal. Retention agreements, equity participation, or thoughtful succession planning can ensure that these key players remain engaged during transitions. Reminder: Their voice at the table also helps owners see practical realities beyond financial projections.

Emotion is an invisible but powerful factor. A founder’s identity is often intertwined with the company’s success. Selling to an outsider can feel like letting go of a family member, while keeping control might bring pride but also prolong financial risk. Employees—many of whom may have been “like family” for decades—can heighten the emotional stakes. Owners naturally worry about their well-being, benefits, and job security when leadership transitions occur. Recognizing these emotions is essential, not as barriers to decision-making, but as signals that values and relationships matter. Reminder: Selling a firm dependent on people is complex and requires significant planning.

The most effective approach is balance: acknowledging emotions without letting them cloud judgment, protecting family harmony while securing financial independence, and honoring the contributions of key employees while positioning the company for sustainable success. A mantra my father shared with me was that “business is people, and your people are the business.” By blending empathy with objectivity, business owners can make decisions that are not only financially sound but also respectful of the human bonds that built the enterprise in the first place. Reminder: Leverage your emotional intelligence and listen intently to hear the subtle messages your team, business and family are telling you.

As business owners enter an ownership transition, it is important to leverage professionals to guide them financially and technically through a complex transaction. More importantly, it is crucial to listen to your family, key employees, and trusted advisors to ensure you know what a successful transaction looks like.

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